| Identification | More | [Name]
4-Aminoindole | [CAS]
5192-23-4 | [Synonyms]
1H-INDOL-4-AMINE
1H-INDOL-4-YLAMINE
4-AMINO-1H-INDOLE
4-INDOLAMINE
INDOLE-4-AMINE
4-Aminoindole
4-Indolamine
5-methoxyl indole-carboxaldehyde
4-AMINOINDOLINE/4-INDOLAMINE
4-Aminoindole ,97% | [EINECS(EC#)]
621-202-0 | [Molecular Formula]
C8H8N2 | [MDL Number]
MFCD01076559 | [Molecular Weight]
132.16 | [MOL File]
5192-23-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Greenish-grey to tan powder | [Melting point ]
106-109 °C (lit.) | [Boiling point ]
354.0±15.0 °C(Predicted) | [density ]
1.268±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C
| [form ]
powder to crystal | [pka]
18.23±0.30(Predicted) | [color ]
White to Gray to Brown | [Water Solubility ]
Insoluble | [Sensitive ]
Air Sensitive | [Detection Methods]
HPLC | [BRN ]
114919 | [InChI]
InChI=1S/C8H8N2/c9-7-2-1-3-8-6(7)4-5-10-8/h1-5,10H,9H2 | [InChIKey]
LUNUNJFSHKSXGQ-UHFFFAOYSA-N | [SMILES]
N1C2=C(C(N)=CC=C2)C=C1 | [CAS DataBase Reference]
5192-23-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [F ]
8-10-34 | [HazardClass ]
AIR SENSITIVE, IRRITANT-HARMFUL, KEEP COLD | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Greenish-grey to tan powder | [Uses]
Reactant for preparation of:• ;Inhibitors of bacterial thymidylate synthase1• ;Mimetics of non-alkaloid toxin lignan anticancer and antiviral agent Podophyllotoxin (PPT)2• ;Inhibitors of Gli1-mediated transcription in the Hedgehog pathway3• ;Protein kinase C θ (PKCθ) inhibitors4• ;Indolic non-peptidic HIV protease inhibitors5• ;Transient receptor potential cation channel subfamily V member 1 (TRPV1) antagonists6• ;Cyclooxygenase-2 (COX-2) and lipoxygenase (LOX) inhibitors7• ;11β-hydroxysteroid dehydrogenase 1 (11β-HSD1) inhibi | [Definition]
ChEBI: 4-Aminoindole is a member of indoles. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 48, p. 5130, 1983 DOI: 10.1021/jo00173a071 | [General Description]
4-Aminoindole is an indole derivative. Its cytokinin activity has been assessed by tobacco pith callus bioassay. 4-Aminoindole can be prepared by reacting 2,6-dinitrotoluene and N,N-dimethylformamide dimethylacetal in anhydrous DMF. | [Synthesis]
A. Synthesis of 4-aminoindole. Iron powder (1.20 g, 21.58 mmol) and acetic acid (2.47 mL, 43.19 mmol) were sequentially added to a solution of ethanol (20 mL) containing 4-nitroindole (1.0 g, 6.17 mmol). The reaction mixture was heated to reflux for 14 hours. After completion of the reaction, the ethanol solvent was removed by rotary evaporator. The residue was dispersed in a solvent mixture of water and ethyl acetate for extraction and separation. The ethyl acetate layer was collected and dried with anhydrous magnesium sulfate followed by filtration to remove the desiccant. The filtrate was concentrated by rotary evaporation to give the crude product. The crude product was further purified by silica gel column chromatography using 1% methanol/dichloromethane mixture as eluent. The elution fractions containing the target product were collected, combined and the solvent was removed by rotary evaporation to give 0.815 g of 4-aminoindole as an orange solid in 82% yield. | [References]
[1] Patent: US6162818, 2000, A |
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